


And the Dreaming

by theprimrosepath



Category: Critical Role (Web Series)
Genre: Comfort, F/M, Friendship/Love, Frumpkin is an Emotional Support Animal (Critical Role), Jester Lavorre Is Not Oblivious, POV Jester Lavorre, Pining Caleb Widogast, Possibly Unrequited Love, Post-Episode c2e100 Hunted at Sea, Widojest Week, brief appearance of Sprinkle
Language: English
Status: Completed
Published: 2020-07-08
Updated: 2020-07-08
Packaged: 2021-03-04 20:00:22
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,181
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25142017
Author URL: https://archiveofourown.org/users/theprimrosepath/pseuds/theprimrosepath
Summary: She was pretty sure that Caleb liked her—like,reallyliked her. Embarrassingly, it'd taken her a while to notice, and part of her still wondered if she was misreading his good friendship into something like a book as she'd done with Fjord.Either way, Caleb always managed to comfort her. Despite every warning Mama had given her, spoken or otherwise, against stymied love, she trusted him.It would be easy to fall in love with Caleb, really. And that kind of scared Jester.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 9
Kudos: 86
Collections: Widojest Week 2020





	And the Dreaming

**Author's Note:**

> i only found out about widojest week like, three days ago? fortunately i'd already started a fic after e100 came out that i could shoehorn the first prompt into pretty easily. (please forgive me for the shoehorning.)
> 
> this ship has gotten so many new works in the past few days <3 love you all.

Caleb was writing in his odd second book. Perfect.

Jester eased down to her knees behind him and dropped her chin on his shoulder. Beneath it, he startled out of his intense concentration, and she couldn't help but giggle despite the unease swirling in her stomach.

"Hello, Jester," said Caleb after a moment.

"Hi, Caleb."

Caleb had slapped shut his book as soon as she put her chin on his shoulder. Jester was still, in general, curious about what exactly was in the book that he kept so private, but she never wanted to push him. Besides, it wasn't why she had searched him out.

He, of course, didn't quite push her either. He exhaled, tapping a finger slowly and softly on the cover of his book, as he set his pen on the floor. He was waiting, she could tell.

Patience was not something that came naturally to Caleb, she had decided a while ago. Oh, he was really good at it, and for as long as she'd known him it was all he exercised, but there was an undercurrent of forced exhaustion to his periods of silence. Like whatever judgments he would have once given voice to were not only faded from a deep weariness but intentionally suppressed. 

The knowledge made Jester sad and a little conflicted. She liked Caleb the way she knew him now. But that was not how he'd always been. And she wanted to hear what he had to say when he was not so weighed down by his secret burdens.

Which made her feel even more guilty about having to ask for reassurance. "So, um. What do you think about this village so far?"

Caleb was trying to sound casual, but Jester could hear his caution. "I think there is a lot more going on than we have seen so far."

"Yeah, it's a really weird place."

Jester sighed and sat back on her heels. At the departure of her weight on his shoulder, Caleb shuffled around until he was facing her. His intent interest soothed her worries, a little bit.

"Like, there's those shadowy cat-things with tentacles, and the mist everywhere, and that flower Yasha ate and she said it was just a little spicy but indigestion kind of sounds like poison to me? Plus there's still that"—Jester hesitated before continuing in a hushed volume—"weird sense of being watched."

At least the grimace on Caleb's face made Jester feel less alone in her anxieties. "Yes. No one else in this village has remarked on it, and no one seems to know the source. It's unsettling to say the least."

Even now, the hairs on the back of Jester's neck still stood on end. She really didn't like the sensation of someone other than the Traveler watching her without even saying hi.

Caleb seemed twitchy now, too, at the topic of conversation. With a snap of his fingers, Frumpkin appeared between them.

Oh, thank the gods. Jester immediately sunk her fingers into his fur.

As she stroked Frumpkin, his tail brushing against her arm, Caleb slid his secret book back into its holster. His gaze did not leave her. "If the feeling worries you, I was already going to suggest to the group that we all sleep with the hut tonight."

"That's a good idea."

Frumpkin meowed and bumped his head against her hand. She gnawed on her lip, trying to figure out how to broach her thoughts.

"You seem preoccupied by something," said Caleb.

Jester's chuckle came out nervous. "Is it obvious?"

"No, but we are friends, _ja_?"

"Yeah." Jester untucked her legs so she could cross them beneath her, sighing as she braced her elbows against her knees and plopped her chin down into a hand. "... You don't happen to have any ideas about what's happening here, do you?"

Caleb considered her question for a long, pensive moment.

As he opened his mouth, though, Jester let some of the words trapped in her throat escape. "It's okay if you don't, it's not really what I'm worried about. Well, it is, but I mean... what if we can't take care of it before TravelerCon?"

"We have handled many things together, Jester. We have faced down an ancient dragon and lived to tell the tale. I doubt there is anything on this island that we cannot take care of, one way or another." 

"Yeah..."

There was another soft meow as Frumpkin crawled into Jester's lap. With a soft chuckle, she adjusted her legs and skirt to make herself a more comfortable place to sit and went back to petting him on the head.

When she looked up again, Caleb's smile made her tilt her head and smile back. He knew what he was doing, and so did she.

An idea struck. Jester ducked her head a little and pulled out Sprinkle from within her hood. The weasel chittered a bit grumpily at the intrusion, but he was amiable enough as she held her beloved pet out to Caleb.

He frowned at the animal in her open hands.

"Just for a little bit, okay? He gets nervous when Frumpkin is too close."

With far more caution than Jester thought was necessary, Caleb took Sprinkle out of her hands. The weasel squirmed in his unsure grip but willingly settled into the nook of his crossed legs as well. There was a moment of reluctance as the man stared down, hands hovering, but Jester didn't want either of them deprived of good company. She gestured at him to get a move on, and slowly he lowered a hand to _very_ gently stroke the animal.

Sprinkle tolerated the affection at least. Pleased, Jester returned to petting Frumpkin. 

"We have time," said Caleb quietly. "Over a week."

Just like that, her worries rippled at her thoughts again like a riptide trying to pull her in. "But what if we don't figure it out before then?"

Everything had to go perfectly. Not because Jester wanted to be the Traveler's number one follower (although that was very important). Not because this was his biggest day yet. And not even because she wanted to keep all those other worshippers safe, though that was kind of important, too. No, this gathering had to go off without a hitch because it was what her best friend wanted. Not only wanted, _needed_. The Traveler had said so—he was getting tired. If he ran, she would go with him, but she didn't want to leave the Mighty Nein if she could help it.

Maybe all of his followers dying (or forgetting about everything, getting a new god, and never leaving this island again) would solve his current problems easily. But Jester figured that was best saved for a backup plan.

Most of all, this opportunity to impress everyone excited her. Maybe that sounded silly. But as much as all this new responsibility frightened her, weighed on her shoulders... she was discovering that it felt good. Good to be trusted. Good to be able to lead a religion—and maybe make people happier, give the people who need it a big laugh.

Caleb had said she needed time to mull it over, and he'd been right. The overwhelming pressure had eased into something bearable, and what Jester wanted now was to live up to it.

Really being here in person, though, with TravelerCon less than two weeks away...

Caleb leaned in, concern furrowing his brow. "Are you afraid, Jester?"

"I'm worried... Maybe a little stressed out?" Jester swallowed down the impulse to tell _someone_ about all of her thoughts. This was not her bedroom at the Chateau with Mama, and Caleb didn't need to worry about more problems that she could handle perfectly well on her own. "We have to host a whole event here— _I_ have to host a whole event here. I don't even know where it could be! That jungle is so thick with no clearings anywhere."

Caleb held up a hand and said, "Slow down, Jester. One thing at a time. First of all, we will figure out how to make this island safe. Together. All of us are here to help you."

She nodded, chewing her lip as Frumpkin pushed his head into her hand.

"Second of all, a lot can happen in a week. I am sure we have plenty of time to prepare for TravelerCon, fight some monsters, and figure out all the set-up. After all." Caleb held up a palm and flame leaped from it. "Creating a clearing ourselves is hardly the toughest thing we have accomplished."

Jester laughed a bit, thinking of blood-sucking demons and assassins who hid in the ground and a cathedral floor strewn with blood, abyssal muck, and shattered glass. "Yeah."

The reassuring smile on Caleb's face warmed her insides in a way that was steadily growing more familiar.

She looked down at Frumpkin and focused on stroking his adorable little head. Not even on purpose, she felt a gentle smile worm its way onto her face. She was pretty sure that Caleb liked her—like, _really_ liked her. Embarrassingly, it'd taken her a while to notice, and part of her still wondered if she was misreading his good friendship into something like a book as she'd done with Fjord.

Either way, Caleb always managed to comfort her. Despite every warning Mama had given her, spoken or otherwise, against stymied love, she trusted him. Yes, he had his demons. But far from burdening her, he'd tried to keep _everyone_ safe from them.

Caleb reminded her much more of Mama than Dad. Always quiet when it mattered, always withdrawn and a little sad inside, always wanting her to be safe—but trusting in her best to stay that way if she ventured in the path of danger.

It would be easy to fall in love with Caleb, really. And that kind of scared Jester.

"You know, we went to a fancy ball, and we didn't even get to dance," she said softly.

She looked up through her lashes to see Caleb blinking at her as if befuddled by the sudden change in topic. Beneath his hand, Sprinkle had curled up into a cozy, fluffy red ball.

"You never actually showed me how well you can waltz," she continued. "You were pretty drunk the one time you tried."

Caleb cleared his throat. "This is not really the best place for a waltz, Jester."

"We're adventurers, Caleb. When do we get a good time to waltz?"

Jester nudged Frumpkin on the shoulder, and after an unwilling moment the cat begrudgingly left her lap. He stretched his back legs as she stood, brushed out her skirts, and held out a hand to Caleb.

He stared, and she wiggled her fingers. "Sprinkle."

Caleb made a silent _oh_ of understanding and carefully scooped up the crimson ferret in his hands. Gratefully, Jester took the drowsy weasel and tucked him back into her hood. Then she held her hand out again.

As begrudgingly as his cat, Caleb accepted her hand and let her pull him to his feet.

"You know, a dance might be really fun to have during TravelerCon," said Jester, and Caleb grimaced. "We're already going to have music. And with your illusion spell, we can make a really pretty atmosphere for dancing. I could use Stone Shape to make a good floor."

"That sounds like a possibility."

"I'm teasing you." Jester patted Caleb's arm, already grinning. The new tone felt much better than her earlier anxiety. "But we should definitely try to have a dance at TravelerCon, and it would be _really_ nice to practice before then so I don't look dumb as the Traveler's high priestess. When will we get another chance?"

Caleb sighed. "We have no music."

"We don't need it." Jester held out her arms expectantly and beamed at him.

As much as she loved to see Caleb smile, his wry expressions were just as good. They were like a silent laugh, at least from him. Obligingly, he stepped closer so they could place their hands in the appropriate positions. Frumpkin weaved through their ankles as they did so, and Jester giggled at the sensation of his soft tail curving around her calves.

The cat looked up toward Caleb and meowed. Jester brought her tail around to gently pat his back with the spade.

"Don't encourage him," said Caleb drily.

"But he's so cute!"

With another plaintive meow, Frumpkin wove through their ankles one last time and trotted off to the side of the small room to sit, tail curling around to rest on his paws.

Jester looked up to see Caleb watching her. She smiled at him through her lashes again, and his cheeks went a little red as his gaze slid away. He cleared his throat again and said, "I suppose I will count us off."

This was exactly what she meant when she thought of him as easy to fall in love with.

"Caleb," said Jester quietly. "Thank you."

He did not meet her eyes, but he replied, "Of course."

**Author's Note:**

> find me at [@primrose-path-of-dalliance](https://primrose-path-of-dalliance.tumblr.com) on tumblr, where i post fandom things and the occasional bit of writing.


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